Dimethylformamide → HCID 10159060, compound

HRID 501034Notes

Reaction equation

HRID 501034 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[N:10]([C:14]([N:19]([CH2:24][CH:25]4[CH2:27][CH2:26]4)[CH2:20][CH:21]4[CH2:23][CH2:22]4)=[C:15]([S:17][CH3:18])[N:16]=3)[CH:11]=[CH:12][N:13]=2)=[C:4]([O:28][CH3:29])[CH:3]=1.C(OCC)(=O)C.[CH3:36][N:37](C)C=O>[C-]#N.[Zn+2].[C-]#N>[CH:21]1([CH2:20][N:19]([CH2:24][CH:25]2[CH2:27][CH2:26]2)[C:14]2[N:10]3[CH:11]=[CH:12][N:13]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([C:36]#[N:37])=[CH:3][C:4]=4[O:28][CH3:29])[C:9]3=[N:16][C:15]=2[S:17][CH3:18])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 22024522HCID 22024522, compound

Product 1

HCID 10159060HCID 10159060, compound

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
95 °C

Procedure

N-[8-(4-Bromo-2-methoxyphenyl)-2-(methylsulfanyl)imidazo[1,2-a]pyrazin-3-yl]-N,N-dicyclopropylmethylamine (53 mg) was dissolved in N,N-dimethylformamide (0.22 mL), then zinc cyanide (23 mg) and tetrakistriphenylphosphine palladium complex (13 mg) were added thereto. After that, the mixture was heated under stirring at 95° C. for 4 hours and cooled to room temperature, and then ethyl acetate was added thereto. The precipitated insoluble matters were filtered off, and then it was extracted with ethyl acetate. The resulting organic layer was washed with water, dried over magnesium sulfate, and then the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:5) to give the title compound (26 mg) as yellow crystals.

Workup

  1. temperatureAfter that, the mixture was heated
  2. temperaturecooled to room temperature
  3. filtrationThe precipitated insoluble matters were filtered off
  4. extractionit was extracted with ethyl acetate
  5. washThe resulting organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was evaporated
  8. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:5)

Sources & evidence

ORD record
ord-662313dc70d04e5280c1a6c50a16d4ec
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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